Exploring mutasynthesis to increase structural diversity in the synthesis of highly oxygenated polyketide lactones.
Org Biomol Chem
; 12(28): 5304-10, 2014 Jul 28.
Article
em En
| MEDLINE
| ID: mdl-24927251
ABSTRACT
The enantioselective synthesis of (2R,3R,4E,8E)-3-hydroxy-2,4,8-trimethyldeca-4,8-dienolide (5) by ring-closing metathesis is described. This compound is an analogue of 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (4) which is a rare 11-membered lactone produced by the fungus, Botrytis cinerea. Mutasynthetic studies with compound 5 using two mutants of B. cinerea led to the isolation of four new highly oxygenated 11-membered lactones (11-14) in which compound 5 has been stereoselectively epoxidized and hydroxylated at sites that were not easily accessible by classical synthetic chemistry.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Botrytis
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Compostos de Epóxi
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Policetídeos
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Lactonas
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article